Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 5-fluoro-1,3-dihydro-2H-indol-2-one | HCID 3731012 | — |
| Reactant | HCID 86618510 | HCID 86618510 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 76798895 | HCID 76798895 | 68% |
Reaction Steps
A solution of 5-fluoro-1,3-dihydro-indol-2-one (1.44 g, 9.54 mmol.) in THF (10 mL) is cooled to 0° C. under an argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (19 mL of a 1 M solution in THF, 19.0 mmol) dropwise. The resulting solution is stirred at 0° C. for 10 min and warmed room temperature. A solution of 6,7-dichloro-1H-furo[3,4-c]pyridin-3-one (1.28 g, 6.27 mmol) in THF (9 mL) is added dropwise to the reaction mixture. The resulting solution is stirred at room temperature for 4 h and the reaction mixture is then poured into aqueous 10% HCl solution (200 mL). The resulting mixture is heated to 90° C. for 2 h and stirred at room temperature for 36 h. The precipitate which formed is collected by filtration, washed with small volumes of ethyl acetate (10×3 mL) and dried under vacuum to give the title compound as a yellow solid (1.43 g, 68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07977351B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-2f72300264f94d2e8c12e35509a60194 |
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| Source note | uspto-grants-2011_07 |
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